Hydroxyamine hydrochloride → 6,8-Dichloro-3-cyanochromone

HRID 2058948Notes

Reaction equation

HRID 2058948 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[O:8][CH:7]=[C:6]([CH:13]=O)[C:5]2=[O:15].Cl.NO.C([NH2:21])=O.[Na]>C(O)=O>[C:13]([C:6]1[C:5](=[O:15])[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=[C:2]([Cl:1])[CH:3]=2)[O:8][CH:7]=1)#[N:21]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 5221296,8-Dichloro-3-formylchromoneHCID 55219744HCID 55219744, compound

Product 1

HCID 7360206,8-Dichloro-3-cyanochromone

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

15 g of 6,8-dichlorochromon-3-aldehyde, 5.43 g of hydroxylamine hydrochloride, 7.55 g of sodium formamide and 100 ml of formic acid are mixed at room temperature and refluxed for 4 hours. After a further 18 hours at room temperature, the precipitate is separated and the filtrate is poured into 1 l of water. The resulting precipitate is filtered off and washed twice with water and twice with ethanol to obtain the heading compound, m.p. 150°.

Workup

  1. temperaturerefluxed for 4 hours
  2. customthe precipitate is separated
  3. additionthe filtrate is poured into 1 l of water
  4. filtrationThe resulting precipitate is filtered off
  5. washwashed twice with water and twice with ethanol
  6. customto obtain the heading compound, m.p. 150°

Sources & evidence

ORD record
ord-9de4f0e7cc904696872c53716bbb491e
Source dataset
uspto-grants-1982_03
Patent number
US04320133

Reaction notes

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